I'm not receiving social security benefits yet, but here's an article about how to legally avoid paying taxes on them. Any thoughts on this? More here.
Making your income nontaxable
For most retirees, the biggest source of taxable income is a retirement savings account, often a traditional IRA or 401(k). The easiest way to convert such income to a nontaxable form is to move it into a Roth account. Roth IRAs are essentially the opposite of traditional IRAs: You don't get a tax break on your contributions, but the money you take out of the account is tax-free. That makes them perfect for retirees looking to reduce their income taxes.
If your retirement date is still a decade or more away, then now is a great time to open up a Roth IRA and start contributing to it. Usually, the best arrangement is to split your contributions between a traditional IRA or 401(k) and a Roth account. That way, you still get a tax break immediately, yet you're also giving yourself some tax-free income in the future. Workers who are fairly close to retirement and are only just opening a Roth IRA will probably want to maximize their Roth contributions to ensure they have a fairly high balance in the account by the time they retire.
On the other hand, if your income is much higher now than you expect it to be after you retire, your best bet is to maximize your contributions to a traditional IRA or 401(k), as that will result in a higher overall tax break. After you retire, you can still move those funds to a Roth account so that they'll produce nontaxable income -- more on that below.
What if I'm already retired?
A retiree or someone close to retirement can still benefit from a Roth account's tax-free income by performing a Roth conversion. That simply means taking money from your traditional IRA or 401(k) and dumping it into a Roth account.
A Roth conversion is a good move if all, or nearly all, of your retirement savings are in a traditional IRA or 401(k), as it would be difficult or impossible to avoid taxes on your Social Security benefits in that scenario. The only problem with a Roth conversion is that you have to pay taxes on the amount you convert, in the year you convert it. That can end up being quite expensive if you have a lot of money to move over. For example, converting $300,000 from your traditional IRA to a Roth IRA all at once would add $82,070.25 to your tax bill for the year (using the 2018 tax brackets for single filers) -- or potentially even more, if you have enough income from other sources to bump you to the top tax bracket.
Instead, it's best to spread a large conversion out over several years to minimize the tax impact, preferably starting a few years before you retire. If you spread your $300,000 conversion out over 10 years, for example, it would cost you just $7,500 per year in extra taxes (assuming you're in the 25% tax bracket after adding the converted funds to your income).
If you're already retired at that point, you'll end up paying taxes on your Social Security benefits during those years (which is another reason why it's best to start converting before you retire), but once the conversion is complete, you'll have gotten rid of those taxes for good.